


Bloody Mary

by RomanGodfrey



Category: Supernatural
Genre: Birthday, Crossdresser, Crossdressing, Drunk Sex, Drunken Shenanigans, Drunkenness, M/M, Makeup, Sam Winchester - Freeform, Trans!Sam, Transgender, Underage - Freeform, Weecest, Wincest - Freeform, boys wearing make up, drunk!Dean, sam wearing makeup, transgender character, transgender!sam
Language: English
Status: Completed
Published: 2015-01-21
Updated: 2015-01-21
Packaged: 2018-03-08 11:41:01
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 1
Words: 2,611
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3207860
Author URL: https://archiveofourown.org/users/RomanGodfrey/pseuds/RomanGodfrey
Summary: <blockquote class="userstuff">
              <p>S01E05 was the inspiration for this, Dean makes Sam play 'Bloody Mary' in the bathroom and rewards him with a lil butt play... </p><p>lmao idk how to write summaries. Wrote this so so so long ago, like two - three years. But I found it on my computer and thought I should post it.</p>
            </blockquote>





	Bloody Mary

_This is stupid_

He ran the head of the match along the box, creating sudden light in the pitch black bathroom. Sam lit the single candle he was allowed and flicked the match into the toilet bowl. It fizzled for a second and then it was again Sam’s breathing in the silence.

His reflection in the mirror was orange and yellow from the dim candle light. He leaned closer to the mirror and swiped away his bangs to look at the obnoxiously large pimple hiding there. It was under the skin and impossible to pop; Sam had tried several times, even called in the help of Dean, but it was still there.

 Sam had waited until Dad went hunting and excused himself from the ever watching gaze of Dean to walk to the nearest drugstore. He had searched in the cosmetics isle for something to hide it for half an hour before a worker walked by for the third time and noticed him looking lost. She asked if she could help, and Sam felt his face flush. He tossed the idea of accepting her help around in his head for a bit before embarrassment and curiosity had gotten the better of him. He was new at this after all, He had mumbled something about hiding his pimples, and she smiled softly. She helped him search and came up with some tube of thick liquid saying ‘base’ on the bottle, mentioning something about her daughter using it.

He paid for it and hurried home. It looked unappealing in the bottle and smelled funny. When he poured some on his fingers it felt greasy. He swiped it across his forehead and it worked for the most part, but it was a little bit darker than his actual skin. He found that if he just put it on the pimple it made it even more obvious; he started by rubbing all around his forehead, and then down his nose and eventually ended up blending it out to past his jaw.

Dean eventually found out; eventually meaning that afternoon when Sam walked through the door carrying a plastic bag. At first he’d been all like “What is it” and then he was like “What the fuck” when Sam explained what it was. Dean warmed up to the idea finally, when Sam told him to fuck off and assured him it was only to cover his blemish.

 He rubbed a finger along his nose smudging out the foundation where his pink skin showed through.  A bump on the side of his nose caught his eye, making him prod and poke it with his finger, absently trying to prod it into a more appealing shape. 

_Still as big as ever_

He pressed his nose into the mirror and Sam sighed against the cool glass, making it weird and foggy. He was just stalling now. Sam jumped and let out an embarrassing squeak at a sudden pounding at the door.

“Hey, Sammy, you doing it yet? I don’t hear you,” Dean yelled through the door with a smile in his voice.

“Shut up, I’m going,”

_I don’t wanna do this, what if she actually shows up?_

“Dean . . .”

“What,”

“What if she actually shows up?”

Dean’s laugh was muffled but Sam still heard it loud and clear. “You’re not gonna pussy out, are you?”

“Fuck you, Dean!”

_It’s just a stupid myth_

_Nothing is gonna happen_

_I just gotta get it over with._

“Bloody Mary.”

Sam had been dumb enough to play truth or dare with Dean but it was Dean’s nineteenth birthday, John was gone hunting, and Dean had drunk a few too many of John’s beers and he was acting the way he did when he was tipsy, almost drunk. His eyes light up and he smiled constantly, laughing at everything. He was always happy when he was drinking.

_Maybe the adrenaline from sneaking around Dad_

Dean had pleaded Sam to play with him, and Sam, like always, couldn’t turn him down.

And now he was in this position. Not wanting to do it but he had to, because that’s what Dean dared him to do; to say Bloody Mary three times in the dark bathroom, and Sam couldn’t not do it. If he didn’t Dean wouldn’t let him hear the last of how he pussyed out.

“Bloody Mary.”

The apartment creaked and groaned and the candle flickered ominously, threatening to go out. Sam felt a cold breathe on his neck; it was coming from behind him.

_What if she’s right behind me?_

_Oh god she’s gonna be right fucking behind me_

Sam’s heart was pounding in his chest but he had to look. He spun around quickly, flinging his arms out to wrap around . . . Thin air.

_She’s invisible?_

_If she’s invisible, it’ll be impossible to fight her_

Sam felt the cold breathe again, this time on his face, coming straight in front of him. He brought up his hands trying to feel for her, ready to strike. He moved his hands back and forth until his fingers touched the wall.

He felt the breathing once more, but there was nothing but wall in front of him. He ran his hands along the wall looking for the source of the ‘breathe’. His fingers met the plastic lining on the really old, really shitty air conditioner that for some reason was attached to the bathroom wall. It didn’t blow out air, it just kind of spurted air, like it was ‘breathing’.

_What the fuck?_

_That’s all it was?_

_I was scared of a fucking heater?_

Sam turned back to the mirror, shaking his head.

_I’m fucking done with this._

_Just a stupid myth._

“Bloody fucking Mary!” He called to the mirror.

_No?_

_Nothing?_

_Wow, what a surprise._

He took one more look at himself and then flung open the door. “Well, De-” He started to announce to the empty hallway. Dean was supposed to be standing right there waiting for him, Sam had been ready to tell him that it was a stupid idea and he hadn’t been the least bit scared, but Dean wasn’t there.

“Uh, Dean?”

Vast shadows were at the end of the short hallway, swallowing the living room. They were coal black and big enough to conceal a full grown man.

_Hiding?_

_Really, Dean?_

Sam walked towards the shadows, playing Deans childish game. He tensed himself, ready for Dean to jump at him; braced himself so as not to flinch. He paused a moment before walking straight out into the shadows, he listened for breathing, shuffling, the stretching of Dean’s jeans. There wasn’t anything; He couldn’t hear him at all.

_Maybe he’s holding his breathe_

_Why would he do that?_

_No, he’s drunk; he wouldn’t think to hold his breathe_

One more step now and Sam would be out in the open, in place to be jumped by Dean. Sam slid his bare foot forward, creating a slight friction that tickled his toes. He scrunched his nose up at the sight of his untrimmed toenails. Sam made a mental note to trim them later, he usually kept them short and filed but he always had to wait for Dad to leave. Sam didn’t want Dad catching him giving himself a pedicure, but Sam couldn’t stop, unkempt toenails bugged the shit out of him. It was almost like an OCD thing for him.

Sam sighed and brought his other foot to meet the one in front; he was now out in the open, waiting for Dean. “Um . . . Dean?” Nothing had happened; no jump attack, no surprise groping, none of the usual ‘Dean’ stuff.

_Where is he?_

_Maybe he went outside,_

_God damn it, the shit probably went outside. Going to go terrorize the neighbors,_

Sam felt along the walling, looking for the light switch and with a flick of his wrist the living room burst into light.

“Well, fuck,”

 Sam saw Dean crouched on all fours at the end of the loveseat. “Dean?”

“I was gonna jump up and surprise you, Sammy,” Dean admitted with a drunk grin on his face. “But you turned on the light.”

“Surprise me? Um, yea . . . not so much of a surprise,”

“Surprise sex!” Dean started to stand, losing his balance half way up and falling back to the floor onto his knees, grunting with the impact.

Sam chuckled. “You were just gonna jump up, surprise me and then fuck me, is that it? Is _that_ why you had me do the stupid bloody Mary thing?

“Maybe . . .” Dean grinned that stupid adorable grin he reserved for Sam only.

“Jerk,” Sam reached out, grabbing Dean’s hand and pulling him up.

Dean tilted his face upward, looking straight into Sam’s eyes. “Look at your pretty eyes . . . They’re so pretty . . . Really pretty . . . And your lips are always so pink-y.” Dean whispered, holding Sam’s chin in his hand and running his thumb over Sam’s bottom lip.

“Oh, are they?” Sam laughed. “ _Are_ my eyes pretty?” Sam’s heartbeat started picking up pace, Dean’s face that close to his, breathe hot and humid and smelling slightly of alcohol, his fingers intertwined with Sam’s, and  Dean’s green eyes were almost nothing but pupil.

“Yea. Yea they are, Sammy.” Dean pressed a light, fleeting kiss to Sam’s mouth and then one each one of his eyelids and then one on the tip of Sam’s nose.

 “Dean, you’re drunk, especially if you’re starting to say girly shit like that.”

Dean smiled and chuckled. “Maybe a little bit… but so what? It’s my birthday,”

“So, you want birthday sex?”

Dean licked his lips, leaving them wet and glossy, before taking hold of Sam’s hair and molding his mouth to Sam’s. Dean’s tongue slipped past Sam’s lips to lick at the top of his mouth, warm and wet. “You, and your fucking gorgeous eyes,” Dean pulled Sam’s head back, exposing his neck to Dean’s mouth. “I really wanna fuck you, right now.” He ran his tongue along Sam’s jaw and down his throat.

“Heh, how does my foundation taste?” Sam sniggered.

“What?” Dean’s voice vibrated against Sam’s skin in a way that made his toes curl.

“Nothing, never mind,” If Dean didn’t taste it then it obviously wasn’t that big of a deal right now, especially because Dean’s mouth was working up Sam’s neck, leaving a trail of kisses and giving Sam butterflies.

Dean brushed Sam’s bottom lip with his tongue and Sam opened his mouth obediently, Sam starting to suck on Dean’s tongue. Dean slid his hands down the back of Sam’s jeans grabbing his ass and grinding onto Sam’s crotch. Sam felt Dean’s hard-on, and Sam wanted nothing else but to be fucked hard right _now._ Sam reached down and palmed Dean’s bulge through his jeans.

Sam’s fingers fumbled with the hem of Dean’s T-shirt, he pulled it over Dean’s head, ruffling Dean’s hair in the process, making random locks of hair stick out in every direction; it was even sexier than before. Dean pulled Sam’s shirt off, popping most of the buttons off. Sam reached for his belt but Dean brushed his hands away, unbuckling Sam himself,  and getting on his knees.

Sam’s pants fell to the ground and then he was standing naked in front of Dean and his eyes ran over Sam, like Sam was the most beautiful thing he had ever seen. It made Sam’s dick twitch, he loved when Dean looked at him like that, like he was the most important thing in the world, like he couldn’t physically take his eyes off him.

Dean kissed Sam’s hipbone, his hand gliding up Sam’s thigh and wrapping around Sam’s cock, Sam biting his lip to stifle the moan. Dean started working him base to tip, twisting his hand around and tightening his grip. He ran his finger over Sam’s slit, and got a spurt of pre-cum in response. Sam gasped when he felt Dean’s tongue wiping it away, and his lips wrap around his dick, sucking him, licking him, and planting kisses on his slit.

Dean swallowed Sam, throat unbelievably tight around the head of his cock and then Dean started to hum, deep in his throat. “Jesus _Christ,_ Dean _!_ ” Dean giggled in response, or as close to a giggle as he could manage with Sam’s cock down his throat.

Dean pulled away, suddenly; Sam whined in protest and grappled for him. “Dean . . .” Sam whined.

Dean, still on his knees, pushed Sam forward and over the arms of the couch. Sam grabbed onto the cushion and he felt Dean spread him wide.  A shudder ran through him when Dean ran his tongue across his sensitive hole. He started kissing the top of Sam’s cheeks and made his ways downwards, licking and kissing, while teasing Sam’s hole with a single finger. The pad of his, forefinger, as best as Sam could tell, rubbed little circles on Sam, before Dean stuck his finger in Sam, up to the first knuckle. He started crooking his finger, brushing Sam’s prostate, making Sam’s hips jerk. Sam felt Dean’s boner rubbing up against his leg and Sam’s dick leaked onto the side of the couch.

Dean brought his tongue to his finger and started licking Sam’s skin around it. He removed his finger and Dean started fucking into Sam with his tongue.  “Dean . . . Oh . . . Oh _shit_ ” Sam moaned into the couch cushion. “Fuck, Dean . . . You said you wanted to fuck me . . . Fuck me, _now._ ”

Dean placed a kiss on the curve of Sam’s ass. “Okay, Sammy,” He nipped at Sam, running his tongue over the tender skin, like he was sugarcoating it. Then Dean’s mouth, hand, fingers, they were gone. The comforting warmth of Dean was there one second and gone the next.

“Dean?”

“Hold on, Sammy, let me get a condom out of my pocket.”

Sam heard the condom packet tear open, the rustle of Dean’s jeans and the sound of Dean sliding the condom on. The head of Dean’s cock brushed Sam’s hole before Dean pushed into him. Stuffed full, Sam moaned into his arm when Dean pulled nearly all the way out and right back in. Dean’s trailed his hand around Sam’s waist, slid his fingers down to Sam’s leaking dick to wrap around it.

Dean wrapped his arm around Sam’s chest, he pulled Sam upright, to hold Sam against his chest as he fucked into him. His thrusts were slower at first, and then he started picking up speed, jerking off Sam to the same rhythm. Sam was breathless; Dean’s mouth on his neck, moaning his name. “Sammy, I’m gonna co- _Oh god,_ Sam,”

Sam reached behind him and grabbed a handful of Dean’s hair. “Dean,” Sam whimpered.  Sam felt Dean’s fingernails dig into his hips, Dean shuddered, repeating Sam’s name and then Sam could feel his brother coming in him. Dean’s lips trailed over Sam’s shoulder and up his neck and Goosebumps raised themselves all over Sam.  

Sam came a second later, fucking into Dean’s hand, ropes of come appearing on the side of the couch. Dean massaged Sam through his orgasm, thrusting into him. Dean slumped over onto Sam, Breathing heavily into his ear.

Sam felt Dean’s come running down his inner thigh, warm and tickly. He took one look at the white mess in front of him and groaned.

“What is it, Sam?” Dean mouthed against Sam’s shoulder blade.

“Look at this mess!”

_I’m going to have to scrub that off_

_Dad’s probably gonna notice a huge wet spot,_

_It’ll dry before he comes home_

_What if it stains?_

“Naw, man . . .” Dean chortled, “It’s like we’re Picasso . . . we painted a picture, Ha!”

Sam groaned again, “Dude, you really are . . . so fucking drunk right now.”


End file.
